Azobenzene C-Nucleosides for Photocontrolled Hybridization of DNA at Room Temperature

• Published in: Chemistry : a European journal Vol. 21; no. 49; pp. 17870 - 17876
• Main Authors: Goldau, Thomas, Murayama, Keiji, Brieke, Clara, Asanuma, Hiroyuki, Heckel, Alexander
• Format: Journal Article
• Language: English
• Published: Weinheim WILEY-VCH Verlag 01.12.2015; WILEY‐VCH Verlag; Wiley Subscription Services, Inc
• Subjects: Amino Alcohols - chemistry; Azo Compounds - chemistry; azobenzene; Base Pairing; Butylene Glycols - chemistry; Chemistry; Control; Deoxyribonucleic acid; Destabilization; DNA; DNA - chemistry; DNA - metabolism; Hybridization, Genetic; Isomerization; Light; Nucleic acids; Nucleosides - chemistry; Nucleosides - metabolism; Photochemistry; photoswitches; Residues; Stability; Temperature; Thermal stability; azobenzene; photoswitches; nucleic acids; photochemistry; DNA
• ISSN: 0947-6539; 1521-3765
• DOI: 10.1002/chem.201503303

Herein, we report the reversible light‐regulated destabilization of DNA duplexes by using azobenzene C‐nucleoside photoswitches. The incorporation of two different azobenzene residues into DNA and their photoswitching properties are described. These new residues demonstrate a photoinduced destabilization effect comparable to the widely applied D‐threoninol‐linked azobenzene switch, which is currently the benchmark. The photoswitches presented herein show excellent photoswitching efficiencies in DNA duplexes – even at room temperature – which are superior to commonly used azobenzene‐based nucleic acid photoswitches. In addition, these photoswitching residues exhibit high thermal stability and excellent fatigue resistance, thus rendering them one of the most efficient candidates for the regulation of duplex stability with light. Powerful light regulation of nucleic acid stability is a challenging task due to the often essential elevated temperatures required for a complete isomerization process. Two different thermally stable and fatigue‐resistant azobenzene C‐nucleosides are introduced into DNA and light‐controlled duplex‐stability regulation at room temperature is demonstrated.